Fancy pants? Not so much. Victoria Hitchcock, a personal stylist to tech execs in Silicon Valley, calls trousers the “worker bees” of men’s wardrobes, reliable yet rarely buzzed about.

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If you’re tired of denim being your only option to fight the chill, consider adding a pair of parachute pants to your winter wardrobe. You can dress them up or down, pairing them with a warm ...